Neighborhoods

Boston bartenders share their wildest Halloween ‘horror stories’

As one bartender put it: "I don’t know if this is Halloween or if somebody’s about to die tonight."

Halloween
Bartenders from Boston share their horror stories. (Jessica Rinaldi/Globe Staff)

If you think your job is scary on Halloween, try being a bartender in Boston.

Not only do they have to serve drinks to ghosts, ghouls, witches, and devils, but they have to deal with the scariest, most unpredictable form of human: inebriated. 

And on a night like Halloween — or the weekends around the holiday — drinking-age adults are on their most frightening behavior. Sure, it’s not the worst holiday to work (that belongs to Mother’s Day and Thanksgiving, according to restaurant employees). But it’s busy, and people are, well, weird when they dress up as evil clowns or a “Storrowed” truck.

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In the spirit of spooky season, Boston.com caught up with local barkeeps who shared their bartending horror stories. 

‘I see this shadow lurking way back, and it’s huge’

“This was in 2003 on a Friday night. I was working that night at [Model]. It’s dark out, and I see this big, tall shadow on the street. It was huge, alright? And it’s kind of reaching out. Then I’m stopping by Tedeschi’s [now the 7/11] before I go into work, and I see this shadow lurking way back, and it’s huge. And it looks like they have something in their hand. I get to work, and somebody’s like ‘There’s someone at the door.’ And I say ‘Absolutely do not let them in.’ It’s this figure I had been seeing all night long. It was 8 feet tall, no exaggeration. [They] can barely get through the door. Grim Reaper, top to bottom, no face. The hands are like skeleton hands, and he has a real scythe, like Children of the Corn-style. It comes in, not saying anything. We’re like ‘Absolutely not.’ You cannot come in here when you have a weapon. I don’t know if this is actually Halloween or if somebody is about to die tonight. For the rest of the night, we’re all on edge. So at the end of the night, I go to my boyfriend’s house, and that f—ing Grim Reaper is inside my boyfriend’s house. It was him the whole f***ing time. He hadn’t told me anything, and he was pissed off that he couldn’t get into the bar.

Sarah Leib, general manager at Silhouette Lounge

Leib’s boyfriend at the time, already tall and lanky, ordered custom-made stilts for the costume. He apparently made a child cry while in costume, according to Leib. 

‘He handed me this scroll with a note on it’

“I was at a bar in the Back Bay, and it was extremely busy. There was a person at the bar, this older guy, and he was really staring at me. I thought it was weird, but he closed out his tab and left. But then he came back two hours later, and he handed me this scroll with a note on it. This was really weird. So I gave it to the bar back to put in the office for me. I don’t even want to look at it. Luckily, he left. But at the end of the night, I had to go look at it. I opened it up, and it was an extremely detailed drawing of me in color. I had blue eyes and freckles on my face [in the drawing]. There was a creepy note asking me to meet up with him, and he gave me his number. Honestly, I probably should have kept it because nobody’s ever drawn a picture of me before. But I immediately threw it away. 

Sarah Heimreid, beverage director at Citrus & Salt and Buttermilk & Bourbon

‘Here I am, covered in alcohol bottles’

“It was in the mid ’90s, and it was at a bar in the Boylston alley. Everyone was decked to the nines Halloween-style — pretty funny stuff, as you can imagine. We’re three deep, busy in the bar. Sometimes behind bars, the way they’re set up is that above the bartender are cabinets where you house your backup alcohol. You can kind of hang [from the cabinets]. What ended up happening in the middle of a shift is that two people got into a tiff. It was really busy, and at that time, you can’t really wait for [security] to come and help out. So I went to grab the cabinetry above to pull myself over the bar, and literally, the cabinets pull out of the ceiling. There’s like 800 people in there, and I go falling backwards, and all the alcohol falls from the cabinets. Everybody stopped, the DJ, the tiff. Here I am, covered in alcohol bottles, and this huge cabinet is just swinging in the breeze, hanging from the ceiling.” 

Willy Shine, beverage director at Seamark

Shine was not injured as a result of nearly 20 bottles of booze falling on or near him. In fact, only six bottles broke because most of them landed on Shine instead of the floor. As for the cabinet, security had to tear it from the wall, the spilled liquor was cleaned up, and in 20 minutes the DJ was spinning, the booze was flowing, and the costumed crowd was dancing. 

‘You’re working probably 14 hours’

“I used to bartend at [Sissy K’s and Wild Rover]. When you work bar crawls, you’re working probably 14 hours. I [had customers] bring me snacks on their trip of the bar crawl. I was like ‘if you could bring me a yerba mate, that would be great.’ So they bring me a yerba mate. Someone brought me gummy bears, a Subway sandwich. Also people don’t know this, but at Sissy K’s in the basement, they have a little kitchen. It’s a [dark] basement, and there happens to be a kitchen down there, and they’re cooking pizzas for [the workers]. I get my pizza, but the only place I can eat it … is literally on a fire escape. 

Asja Mehmedovic, part-time bartender

Mehmedovic said there was actually more room to eat her pizza on the fire escape, where she sat with her knees up, than inside the busy bar. She had not known the fire escape existed until that evening, and she certainly didn’t think anyone could take a meal break on it. 

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Katelyn Umholtz

Food and Restaurant Reporter

Katelyn Umholtz covers food and restaurants for Boston.com. Katelyn is also the author of The Dish, a weekly food newsletter.

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